Form 4: Oscar Health CEO Sells Shares for Tax Withholding

Oscar Health CEO Mark Bertolini sold company stock to cover tax obligations related to vested stock units, executing a pre-planned Rule 10b5-1 trading plan.

Summary

• Mark Bertolini, CEO of Oscar Health, Inc., reported the sale of company stock on June 25th and June 26th, 2026.
• These sales were conducted to satisfy tax withholding obligations arising from the settlement of performance and time-based restricted stock units that vested on April 3, 2026.
• The transactions were executed under a Rule 10b5-1 trading plan, initially entered into on November 10, 2025, and subsequently amended and restated on March 24, 2026.
• A total of 708,713 shares were sold across multiple transactions at weighted average prices ranging from $28.06 to $30.17.
• Following these transactions, Bertolini beneficially owns 8,990,566 shares of Class A Common Stock.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral event. While insider selling can be a negative signal, the clear explanation of tax withholding and the use of a pre-established Rule 10b5-1 plan mitigate concerns about adverse market impact.

Negatives

• The CEO sold a significant number of shares, which could be perceived negatively by the market, although it was for tax purposes.
• The weighted average sale prices indicate a range of values at which the shares were disposed of.

Risks

• The sale of shares by a key executive could be interpreted as a lack of confidence in the company's future performance, despite being for tax purposes.
• The weighted average pricing suggests that shares were sold at various price points, which might indicate market fluctuations during the transaction period.

Future Outlook

The filing does not contain forward-looking statements or guidance. It reports on past transactions.

Management Comments

• The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026.
• The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

Industry Context

StockSavvy.ai notes that insider sales, particularly by CEOs, are common for managing tax liabilities associated with equity compensation. The use of a Rule 10b5-1 plan indicates a structured approach to these sales, designed to avoid accusations of insider trading.

Stakeholder Impact

• Shareholders: May interpret the sale as a negative signal, though the tax-related nature and Rule 10b5-1 plan should provide context.
• Employees: The sale by the CEO might influence employee sentiment regarding stock ownership.
• Management: Demonstrates adherence to established trading plans for managing equity compensation.

Next Steps

• The reporting person may be required to provide further details on specific sale prices upon request from the Issuer, security holders, or the SEC staff.

Key Dates

Keywords

Oscar Health, OSCR, Form 4, Insider Trading, Stock Sale, CEO, Mark Bertolini, Tax Withholding, Rule 10b5-1, Restricted Stock Units, Vesting